ChemicalBook > CAS DataBase List > YHO-13177

YHO-13177

Product Name: YHO-13177
CAS No.: 912287-56-0
Chemical Name: YHO-13177
Synonyms: CS-2881;YHO-13177;YHO-13177, 10 mM in DMSO;BCRP Inhibitor III, YHO-13177;BCRP,YHO-13177,Inhibitor,ABCG2,Breast cancer resistance protein,inhibit;(Z)-2-(3,4-Dimethoxyphenyl)-3-(5-(4-hydroxypiperidin-1-yl)thiophen-2-yl)acrylonitrile;Benzeneacetonitrile, α-[[5-(4-hydroxy-1-piperidinyl)-2-thienyl]methylene]-3,4-dimethoxy-, (αZ)-
CBNumber: CB83035212
Molecular Formula: C20H22N2O3S
Formula Weight: 370.47
MOL File: 912287-56-0.mol

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YHO-13177 Property

Boiling point:: 577.4±50.0 °C(Predicted)
Density: 1.266±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO: 100mg/mL
form: Solid
pka: 14.78±0.20(Predicted)
color: Light yellow to yellow

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

ChemScene

Product number: CS-3968
Product name: YHO-13177
Purity: 98.40%
Packaging: 5mg
Price: $100
Updated: 2021/12/16

ChemScene

Product number: CS-3968
Product name: YHO-13177
Purity: 98.40%
Packaging: 10mg
Price: $150
Updated: 2021/12/16

ChemScene

Product number: CS-3968
Product name: YHO-13177
Purity: 98.40%
Packaging: 50mg
Price: $450
Updated: 2021/12/16

ChemScene

Product number: CS-3968
Product name: YHO-13177
Purity: 98.40%
Packaging: 100mg
Price: $750
Updated: 2021/12/16

DC Chemicals

Product number: DC9369
Product name: YHO-13177
Purity: >98%
Packaging: 100mg
Price: $450
Updated: 2021/12/16

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YHO-13177 Chemical Properties,Usage,Production

Uses

YHO-13177, a acrylonitrile derivative, is an orally active, potent and specific inhibitor of breast cancer resistance protein (BCRP) and ABCG2 with an IC50 value of 10 nM. YHO-13177 potentiates the cytotoxicity of SN-38 in HCT116 and A549 cells that express BCRP. YHO-13177 combined with Irinotecan (HY-16562) significantly suppresses the tumor growth in an HCT116/BCRP xenograft model[1][2][3].

Synthesis

93-17-4

207290-72-0

912287-56-0

GENERAL STEPS: 5-(4-hydroxypiperidin-1-yl)-2-thiophenecarboxaldehyde and 3,4-dimethoxybenzeneacetonitrile were placed in a reactor and dissolved in ethanol. After addition of sodium ethoxide, the mixture was stirred under reflux conditions. After completion of the reaction, the reaction mixture was cooled with flowing water for tens of minutes. Water was added to the cooled mixture and stirring was continued for tens of minutes. The precipitated crystals were collected by filtration, washed sequentially with water, ethanol and hexane, and then dried under reduced pressure to give (Z)-2-(3,4-dimethoxyphenyl)-3-[5-(4-hydroxypiperidin-1-yl)thiophen-2-yl]acrylonitrile. Using 5-bromothiophene-2-carbaldehyde (42.30 g) and 4-hydroxypiperidine (67.30 g), an amination reaction was carried out according to Preparation Step 1 to obtain 5-(4-hydroxypiperidin-1-yl)-2-thiophenecarboxaldehyde (yield: 33.00 g, 71%). The prepared 5-(4-hydroxypiperidin-1-yl)-2-thiophenecarboxaldehyde (10.56 g) was subjected to condensation reaction with 3,4-dimethoxyphenylacetonitrile (8.86 g) according to the preparation step 2 to obtain (Z)-2-(3,4-dimethoxyphenyl)-3-[5-(4-hydroxypiperidin-1-yl)thiophen-2-yl]acrylonitrile (yield: 13.50 g, 73%). The obtained (Z)-2-(3,4-dimethoxyphenyl)-3-[5-(4-hydroxypiperidin-1-yl)thiophen-2-yl]acrylonitrile (20.00 g) was dissolved in chloroform (650 mL), and reacted with pyridine (6.41 g) and bromoacetyl bromide (14.13 g) according to Preparation Step 3 (Method A) to obtain bromoacetic acid 1-[5-[(Z)-2- cyano-2 -(3,4-dimethoxyphenyl)vinyl]thiophen-2-yl]piperidin-4-yl ester (yield: 23.00 g, 87%). The prepared 1-[5-[(Z)-2-cyano-2-(3,4-dimethoxyphenyl)vinyl]thiophen-2-yl]piperidin-4-yl ester of bromoacetic acid (2.30 g) was dissolved in chloroform (100 mL), and was reacted with piperidine (533 mg) and triethylamine (658 mg) according to Preparation Step 4 to give (Z)-2-(3,4-dimethoxyphenyl)-3-(5 -(4-hydroxypiperidin-1-yl)thiophen-2-yl)acrylonitrile (Yield: 1.40 g, 60%).

in vivo

YHO-13177 (19.7μM, i.v., or 27.3μM, p.o., a single dose for 25 days) is converted by YHO-13351, increases the survival time of mice inoculated with BCRP-transduced murine leukemia P388 cells and suppresses the tumor growth in an HCT116/BCRP xenograft mouse model^[1].

Animal Model:	HCT116/BCRP xenograft mouse model^[1]
Dosage:	19.7 μM or 27.3 μM
Administration:	19.7 μM, i.v., or 27.3 μM, p.o., a single dose for 25 days
Result:	Was maintained for at least 8 hours in plasma.

References

[1] Yamazaki R, et al. Novel acrylonitrile derivatives, YHO-13177 and YHO-13351, reverse BCRP/ABCG2-mediated drug resistance in vitro and in vivo. Mol Cancer Ther. 2011 Jul;10(7):1252-63. DOI:10.1158/1535-7163.MCT-10-0874
[2] Shishido Y, et al. ABCG2 inhibitor YHO-13351 sensitizes cancer stem/initiating-like side population cells to irinotecan. Anticancer Res. 2013 Apr;33(4):1379-86. PMID:23564776
[3] Yu S, et al. The mechanisms of multidrug resistance of breast cancer and research progress on related reversal agents. Bioorg Med Chem. 2023 Nov 15;95:117486. DOI:10.1016/j.bmc.2023.117486

YHO-13177 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from YHO-13177 manufacturers

Career Henan Chemical Co

Product: YHO-13177 912287-56-0
Price: US $1.00/g
Min. Order: 1g
Purity: 99%
Supply Ability: 200kg
Release date: 2019-12-25

912287-56-0, YHO-13177Related Search:

YHO-13351 (free base) YHO-13351

YHO-13177

CS-2881

Benzeneacetonitrile, α-[[5-(4-hydroxy-1-piperidinyl)-2-thienyl]methylene]-3,4-dimethoxy-, (αZ)-

(Z)-2-(3,4-Dimethoxyphenyl)-3-(5-(4-hydroxypiperidin-1-yl)thiophen-2-yl)acrylonitrile

BCRP,YHO-13177,Inhibitor,ABCG2,Breast cancer resistance protein,inhibit

YHO-13177, 10 mM in DMSO

BCRP Inhibitor III, YHO-13177

912287-56-0